Abstract
Rat liver cytosolic 3α-hydroxysteroid dehydrogenase (EC 1.1.1.50) (dihydrodiol dehydrogenase) which can catalyze the conversion between androsterone and androstanedione in the presence of NADP(H) has also been shown to catalyze the oxidation of benzenedihydrodiol to catechol (Penning et al, 1984, 1985; Hara et al., 1988). From the facts that can oxidize the trans-dihydrodiol of polycyclic aromatic hydrocarbons such as benzo(a)pyrene and benzo(a)anthracene, it has been suggested that dihydrodiol dehydrogenase plays an important role in the detoxification of the polycyclic aromatic hydrocarbon through the effective suppression in the formation of the ultimate carcinogenic anti-diol epoxides (Penning et al., 1984, 1985).
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References
Cappel.R.E. and Gilbert,H.F.,1986, Cooperative behavior in the thiol oxidation of rabbit muscle glycogen Phosphorylase in cysteamine-cystamine redox buffers, J.Biol.Chem., 261:15378
Everson,R.B.,Randerath,E.,Santella,R.M.,Cefalo,R.C.,Avitts,T.A. and Randerath.K.,1986, Detection of smoking-related covalent DNA adducts in human placenta, Science, 231:54
Flynn,T.G.,1982, Aldehyde reductase : monomeric NADPH-dependent oxidoreductases with multifunctional potential, Biochem.Pharmacol., 31:2705
Turner,A.J. and Flynn,T.G.,1982, The nomenclature of aldehyde reductases, in : “Enzymology of Carbonyl Metabolism: Aldehyde dehydrogenase, aldoketo reductase, alcohol dehydrogenase,”, H.Weiner and B.Wermuth, eds., Alan R. Liss, New York
Glatt,H.R.,Vogel,K.,Bentley,P. and Oesch,F.,1979,Reduction of benzo(a)- pyrene mutagenicity by dihydrodiol dehydrogenase, Nature, 277:319
Hara,A.,Inoue,Y.,Nakagawa,M.,Naganeo,F. and Sawada,H.,1988, Purification and characterization of NADP-dependent 3-hydroxysteroid dehydrogenase from mouse liver cytosol, J.Biochem., 103:1027
Hatakeyama,M.,Tanimoto,Y. and Mizoguchi,T., 1984, Purification and some properties of bovine liver cytosol thioltransferase, J.Biochem., 95:1811
Hatakeyama.M.,Lee,C.,Chon,C.,Hayashi,M.and Mizoguchi,T.,1985, Purification and some properties of rabbit liver cytosol thioltransferase, J.Biochem., 97:893
Ikeda,M.,Hattori,H. and Ohmori,S.,1984, Properties of NADPH-dependent carbonyl reductases in rat liver cytosol, Biochem.Pharmacol., 33:3957
Keller,G.M. and Jefcoate,C.R.,1984, Kinetic determinants of benzo(a)pyrene metabolism to dihydrodiol epoxides by 3-raethylcholanthrene induced rat liver microsomes, Mol.Pharmacol., 22:451
Kosower,N.S.,1978,The glutathione status of cells, Int.Rev.Cytol.,54:109
Mizoguchi.T.,Uchida,G.,Oshida,T.,Terada,T. and Hosomi,S.,1988, Changes in mice liver thioltransferase activity and powerful inhibitors, in : “Glutathione Centennial” 114
Morrison,H.,Hammorskiold,V. and Jernstrom,B.,1983, Status of reduced glutathione in primary cultures of rat hepatocytes and the effect on conjugation of benzo(a)pyrene 7,8-dihydrodiol 9,10-epoxide, Chem-Biol.Interactions, 45:235
Ness,G.C.,McCreery,M.J.,Sample,C.E.,Smith,M. and Pendleton,L.C.,1985, Sulfhydryl-disulfide forms of rat liver 3-hydroxy 3-methylglutaryl coenzyme A reductase, J.Biol.Chem., 260:16395
Nishinaka.T.,Terada,T.,Umemura,T.,Nanjo,H.,Mizoguchi,T.and Nishihara,T., Study on dihydrodiol dehydrogenase (I) Molecular forms of the enzyme and the presence of a dihydrodiol specific enzyme in bovine liver cytosol, in: “Enzymology of Carbonyl Metabolism : Aldehyde dehydrogenase, aldo-keto reductase, alcohol dehydrogenase”,in press
Oshida,T.,Maeda,H.,Hara,T.,Terada,T.,Hosomi,S.,Mizoguchi,T. and Nishihara, T.,1989, Human thioltransferase : Its purification and physiological role, J.Pharmacobio-Dyn., 12:s-52
Penning,T.M.,Mulcharji,I.,Barrows,S. and Talaley,P.,1984, Purification and properties of a 3-hydroxysteroid dehydrogenase EC 1.1.1.50 of rat liver cytosol and its inhibition by anti-inflammatory drugs, Biochem.J., 222:601
Penning,T.M.,Sharp,R.B. and Krieger,N.R.,1985, Purification and properties of 3-hydroxysteroid dehydrogenase from rat brain cytosol inhibition by nonsteroidal anti-inflammatory drugs and progestins, J.Biol.Chem., 260:15266
Piatt,K.L. and Oesch,F.,1977, An improved synthesis of trans-5,6-dihydroxy- 1,3-cyclohexadiene, Synthesis, 7:449
Smithgall,T.E.,Harvey,R.G. and Penning,T.M.,1986, Regio- and stereospecificity of homogeneous 3-hydroxysteroid-dihydrodiol dehydrogenase for trans-dihydrodiol metabolites of polycyclic aromatic hydrocarbons, J.Biol.Chem., 261:6184
Sugiyama,T.,1988, Modification of enzyme activity by glutathione, Protein Nucleic Acid and Enzyme (in Japanese), 33:1423
Taniguchi,N., 1986, Modification of enzyme protein by glutathione, Metabolism and Disease (in Japanese), 23:1057
Vogel.K.,Bentley,P.,Piatt,K.L. and Oesch,F.,1980, Rat liver cytoplasmic dihydrodiol dehydrogenase. Purification and apparent homogeneity and properties, J.Biol.Chem., 255:9621
Vina,J.,Hems,R. and Krebs,H.A.,1978, Maintenance of glutathione content in isolated hepatocytes, Biochem.J., 170:627
Wallin,R.,1979, Some molecular properties of NAD(P)H dehydrogenase from rat liver, Biochem.J., 181:127
Walters,D.W. and Gilbert,H.F.,1986, Thiol-disulfide redox equilibrium andkinetic behavior of chicken liver fatty-acid synthase, J.Biol.Chem. 261:13135
Watabe,T. and Hiratsuka.A.,1988, Glutathione cojugation reactions: Metabolic inactivation and activation of carcinogens and other toxicants by glutathione s-transferase, Protein Nucleic Acid and Enzyme (in Japanese), 33:1405
Wermuth.B.,Platt,K.L.,Seidel,A and Oesch,F.,1986, Carbonyl reductase provides the enzymatic basis of quinone detoxication in man, Biochem.Pharmcol., 35:1277
Ziegler,D.M.,1985, Role of reversible oxidation-reduction of enzyme thiol-disulfides in metabolic regulation, Ann.Rev.Biochem., 54:305
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© 1990 Plenum Press, New York
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Terada, T. et al. (1990). Study on Dihydrodiol Dehydrogenase (II) Modulation of Dihydrodiol Dehydrogenase Activity by Biological Disulfides. In: Weiner, H., Wermuth, B., Crabb, D.W. (eds) Enzymology and Molecular Biology of Carbonyl Metabolism 3. Advances in Experimental Medicine and Biology, vol 284. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-5901-2_20
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DOI: https://doi.org/10.1007/978-1-4684-5901-2_20
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